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Burns, N. Z.; Jacobsen, E. N., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 830.
Jacobsen has reported an acyl-Mannich reaction of isoquinolines with O-tert-butyldimethylsilyl O′-isopropyl ketene acetal 7 catalyzed by thiourea 117 (Scheme 43).[65] The heterocycle is premixed with 2,2,2-trichloroethyl chloroformate and then treated with catalyst and nucleophile to yield enantioenriched 1-substituted dihydroisoquinoline 118. Several substituted isoquinolines are also reported as viable substrates for this transformation. The enamide in 118 can be readily reduced with triethylsilane and trifluoroacetic acid to give the tetrahydroisoquinoline.
Meeeee 88 Meeeeeee-Meeeeeeee Meeeeeee ee Meeeeeeeeeee[88]
Meeeeee eee eeeeeeee ee eeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeee 888 ee eeeeeeee ee eeeeeeeeeee eeeeeeee eeeee e eeeeeeeeee eeeeeeeee(MM)–MMMMMMM eeeeeeee 888 (Meeeee 88).[88] Me ee eeeeeeeee ee eeeeee eee eeeeeeee eeeeeeee eeee ee-eeee-eeeee eeeeeeeeeee, eee eeeeeeeeeee eeeeeee[88] eeee eeeee eeee ee eeeeeeeeeeee M-eeeeeeeee 8-eeee-eeeee eeeeeeeee eeeeeee ee eeeeee, eeeee eeeeeeeee eeeeeeeeeeeeeee ee eee eeee-eeeee eeeeee ee eee eeeeeeee ee eeeeeeee eee eeee eeeeeee eeee ee eeee-eeeee eeeeeee ee eeee ee eeeeeeeeeeeee eeeeeee eeeeeeeeeeeeeeeeeeeeeeeee. Mee eeeeeeeeeeee eeeeeee ee eeeeeee ee ee e eeeeeeeee eeeeeee. Meee 8.8–8 eee% eeeeeeee ee eeeeeeeee ee eeeeeee eeeeeeeee ee 888 eeee eeee eeeee (>88% ee eeee eeeee) eee eeeeeeeeeeeeeeeeee. Meee ee eee eeeeeeee eeeeeeeeee eee eeeeeeee-eeee eeeeeee-eeeeeeeeeee eeeeeeeeeeeeeeeeeeee.
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeee Me Meee Meeeeeeeeeeeeeeeeeeeeee[88]
| M8 | M8 | M8 | M8 | ee (%) | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| M | MMe | MMe | M | 88 | 88 | [88] |
| M | M | M | M | 88 | 88 | [88] |
| MMe | MMe | M | M | 88 | 88 | [88] |
| MMe | M | M | MMe | 88 | 88 | [88] |
| M | M | Me | M | 88 | 88 | [88] |
| M | M | Me | M | 88 | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee (M)-8-[8-(eeee-Meeeeeeeeeeeee)-8,8-eeeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeeee-8-ee]eeeeeeee (888, M8 = M8 = M; M8 = M8 = MMe); Meeeeee Meeeeeeee:[88]
Mee eeeee 888 (M8 = M8 = M; M8 = M8 = MMe; 888 ee, 8.88 eeee) eee Mee8M (888 ee, 8.88 eeee, 8.8 eeeee) eeee eeeeeeeee ee MM8Me8 (8.8 eM). Mee eeeeeeeee eeeeeee eee eeeeeee eee 88 eee ee eeeeeee eeeeeeeeeee. Meeee eee-eeee eeeeeee, eeeeeeeeeee eeeeeeee (888 µM, 8.88 eeee, 8.8 eeeee) eee eee Me eeeeeee 888 (88.8 ee, 8.8888 eeee, 8 eee%) eeee eeeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeee ee eee eeee eeeeeeeeeee eee ee eeeeeeeeee 8 e. Meeee eeeeeeeeee ee eee eeeeeeee, MeMMe (8 eM) eee eeeee (8 eM) eeee eeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee, eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe ee eeeeee/Me8M) eeeeeeee e eeeee eeeee; eeeee: 888 ee (88%); 88% ee (eeeeeeeeee ee eeeeee MMMM).
References
| [65] | Meeeee, M. M.; Meeeeeee, M.; Meeeeeee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [66] | Meeeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [67] | Meee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeee, M. M.; Meeeee, M.; Meeeeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88M/8, 888.
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